You can look at **[Omnifocus][1]** (a task management app), which has a repeat task option. They split it into two dropdowns once you select Repeat monthly. **Option 1: select specific days for the month:** [![enter image description here][2]][2] **Option 2: select days of the week for each month** [![enter image description here][3]][3] ###Update: Another option - make it read like a sentence### You could also make the form to read like a sentence. [![enter image description here][4]][4] [1]: https://www.omnigroup.com/omnifocus [2]: https://i.sstatic.net/H6huB.png [3]: https://i.sstatic.net/313cq.png [4]: https://i.sstatic.net/IXuhl.png